Electrochemical vicinal oxyazidation of α-arylvinyl acetates

Yi-Lun Li; Zhaojiang Shi; Tao Shen; Ke-Yin Ye

doi:10.3762/bjoc.18.103

Electrochemical vicinal oxyazidation of α-arylvinyl acetates

Beilstein J Org Chem. 2022 Aug 12:18:1026-1031. doi: 10.3762/bjoc.18.103. eCollection 2022.

Authors

Yi-Lun Li¹, Zhaojiang Shi¹, Tao Shen², Ke-Yin Ye¹

Affiliations

¹ Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China.
² Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China.

Abstract

α-Azidoketones are valuable and versatile building blocks in the synthesis of various bioactive small molecules. Herein, we describe an environmentally friendly and efficient electrochemical vicinal oxyazidation protocol of α-arylvinyl acetates to afford diverse α-azidoketones in good yields without the use of a stoichiometric amount of chemical oxidant. A range of functionality is shown to be compatible with this transformation, and further applications are demonstrated.

Keywords: azide; azidoketone; electrosynthesis; enol acetate; radical.

Grants and funding

Financial support from the National Natural Science Foundation of China (22071025, 21901041), State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University (202008), Hundred-Talent Project of Fujian (50012742), and Fuzhou University (510841) is gratefully acknowledged.